Compound Detail

CHEMBL11

IMIPRAMINE

💊 Approved Drug

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💊 Approved Drug

CN(C)CCCN1c2ccccc2CCc2ccccc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL11
Name	IMIPRAMINE
Phase	Approved
Structure Type	MOL
InChI Key	BCGWQEUPMDMJNV-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Antideprin Berkomine Cristalia Imipramina Imipramine Melipramine NSC-169866 ORG-2463 Sermonil Trimipramine maleate impurity, imipramine-

Targets

143

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

280.4

MW (Da)

3.88

ALogP

HBA

HBD

6.5

PSA (Å²)

0.84

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1959
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product

USAN Stem

-pramine

Extended Properties

Molecular Formula	C19H24N2
MW	280.42
Aromatic Rings	2
Heavy Atoms	21
NP-Likeness	-0.77

Indications

Depressive Disorder Depressive Disorder Anxiety Chest Pain Death, Sudden, Cardiac Dementia Digestive System Diseases Gastroesophageal Reflux Low Back Pain Myocardial Infarction Schizophrenia Urinary Incontinence, Stress Ventricular Fibrillation Rosacea Somatoform Disorders Dysthymic Disorder Photosensitivity Disorders Breast Neoplasms

ATC Classification

N06AA02

imipramine

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 92 meas. best 10.22

Ki 45 meas. best 9.28

EC50 4 meas. best 6.52

Kd 2 meas. best 8.9

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histamine H1 receptor CHEMBL4701	IC50	10.22	10.22	0.1	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	9.28	8.2944	0.5	16
Sodium-dependent serotonin transporter CHEMBL228	IC50	9.06	8.368	0.9	15
Serotonin (5-HT) receptor CHEMBL2096904	Ki	8.96	8.96	1.1	1
Serotonin (5-HT) receptor CHEMBL2096904	IC50	8.96	8.96	1.1	1
Ileum CHEMBL613680	Kd	8.9	8.9	1.3	1
Alpha-1A adrenergic receptor CHEMBL319	IC50	8.77	8.77	1.7	1
Sodium-dependent serotonin transporter CHEMBL4642	Ki	8.3	7.84	5.0	2
Histamine H1 receptor CHEMBL231	Ki	8.0	8.0	10.0	1
Unchecked CHEMBL612545	Ki	7.92	7.1733	12.0	3
Norepinephrine transporter CHEMBL304	Ki	7.92	7.92	12.0	1
Sodium-dependent noradrenaline transporter CHEMBL2370	Ki	7.92	7.86	12.0	2
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	7.8	7.8	16.0	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	7.64	7.64	23.0	1
Histamine H1 receptor CHEMBL231	IC50	7.57	7.57	27.0	1
Rattus norvegicus CHEMBL376	IC50	7.57	6.2895	27.0	19
Sodium-dependent serotonin transporter CHEMBL313	Ki	7.54	7.4867	29.0	3
Unchecked CHEMBL612545	IC50	7.52	6.054	30.0	5
Serotonin (5-HT) receptor CHEMBL2094123	IC50	7.36	7.36	44.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	7.34	7.0	46.0	2
Norepinephrine transporter CHEMBL304	IC50	7.22	6.5633	60.0	3
Sodium-dependent serotonin transporter CHEMBL313	IC50	7.21	6.685	61.0	4
Muscarinic acetylcholine receptor CHEMBL1907609	Ki	7.19	7.19	65.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	7.13	7.13	74.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	7.03	6.915	94.0	2
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.8	6.8	160.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	IC50	6.8	6.8	160.0	1
5-hydroxytryptamine receptor 2C CHEMBL3006	Ki	6.8	6.8	160.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	6.66	6.66	220.0	1
Adrenergic receptor alpha-2 CHEMBL2093864	Ki	6.59	5.95	255.0	2
Muscarinic acetylcholine receptor CHEMBL1907609	IC50	6.57	6.57	269.0	1
Mus musculus CHEMBL375	EC50	6.52	6.205	300.0	2
Muscarinic acetylcholine receptor M5 CHEMBL277	IC50	6.52	6.52	300.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL3602	Ki	6.46	6.46	343.0	1
D(2) dopamine receptor CHEMBL217	IC50	6.39	6.39	410.0	1
Solute carrier family 22 member 2 CHEMBL1743122	IC50	6.22	6.22	600.0	1
Dopamine receptor CHEMBL2093868	IC50	6.19	6.19	645.0	1
D(2) dopamine receptor CHEMBL3427	Ki	6.14	6.14	726.0	1
D(2) dopamine receptor CHEMBL217	Ki	6.14	6.14	726.0	1
Histamine H2 receptor CHEMBL2882	IC50	5.72	5.72	1900.0	1
Sigma intracellular receptor 2 CHEMBL4105864	Ki	5.68	5.68	2107.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.47	5.47	3388.4	8
Sodium channel alpha subunit CHEMBL2331043	IC50	5.44	5.44	3600.0	1
Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2096682	IC50	5.44	5.44	3600.0	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL3762	IC50	5.39	5.235	4050.0	2
Sphingomyelin phosphodiesterase CHEMBL2760	IC50	5.3	5.3	5000.0	1
ScN2a CHEMBL613872	EC50	5.3	5.3	5000.0	1
Solute carrier family 22 member 1 CHEMBL5685	IC50	5.1	4.7667	7950.0	3
Voltage-gated L-type calcium channel CHEMBL2095229	IC50	5.08	5.08	8300.0	1
Major prion protein CHEMBL4869	EC50	5.0	5.0	10000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	9.46	mL.min-1.kg-1	Homo sapiens
CL	13.0	mL.min-1.kg-1	Homo sapiens
CL	13.0	mL.min-1.kg-1	Homo sapiens
CL	5.62	uL.min-1.(10^6cells)-1	Homo sapiens
CL	13.49	mL.min-1.g-1	Homo sapiens
CL	150.0	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	1.2e-05	mL.min-1.g-1	Homo sapiens
CL	-	-	Homo sapiens
CL	299.0	mL.min-1.kg-1	Homo sapiens
CL	86.8	uL.min-1.(10^6cells)-1	Homo sapiens
CL	23.6	uL.min-1.(10^6cells)-1	Homo sapiens
CL	13.5	mL.min-1.kg-1	Homo sapiens
CL	0.012	uL/min	Homo sapiens
CL	0.038	mL.min-1.g-1	Homo sapiens
CL	0.038	mL.min-1.g-1	Homo sapiens
CL	0.038	mL.min-1.g-1	Homo sapiens
CL	0.0511	mL.min-1.g-1	Homo sapiens
CL	0.0396	mL.min-1.g-1	Homo sapiens
CL	115.5	mL.min-1.g-1	Homo sapiens
CL	79.5	mL.min-1.g-1	Homo sapiens
CL	125.5	mL.min-1.g-1	Mus musculus
CL	616.9	mL.min-1.kg-1	Homo sapiens
CL	202.0	mL.min-1.g-1	Mus musculus
CL	687.0	mL.min-1.kg-1	Mus musculus
CL	7.8	mL.min-1.g-1	Homo sapiens
CL	115.0	mL.min-1.g-1	Homo sapiens
CL	22.8	mL.min-1.g-1	Homo sapiens
CL	113.7	mL.min-1.g-1	Rattus norvegicus
CL	104.1	mL.min-1.g-1	Rattus norvegicus
Cmax	710.0	nM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histamine H1 receptor	IC50	=	0.06	nM	10.22	Compound tested for its inhibitory activity against Histamine H1 receptor	10447960
Sodium-dependent serotonin transporter	Ki	=	0.52	nM	9.28	Binding affinity to human 5-HT transporter by radioligand displacement assay	23466604
Sodium-dependent serotonin transporter	Ki	=	0.77	nM	9.11	Displacement of [3H]imipramine from human 5HT transporter	21726069
Sodium-dependent serotonin transporter	IC50	=	0.88	nM	9.06	Displacement of [3H]imipramine from human recombinant 5-HT transporter expressed...	26988801
Sodium-dependent serotonin transporter	IC50	=	0.88	nM	9.06	Displacement of [3H]imipramine from human recombinant 5HT transporter expressed ...	27876250
Sodium-dependent serotonin transporter	Ki	=	1.0	nM	9.0	Displacement of [3H]-imipramine from human serotonin transporter expressed in HE...	28763213
Serotonin (5-HT) receptor	Ki	=	1.1	nM	8.96	Binding affinity to 5HT receptor (unknown origin) assessed as inhibition constan...	28849908
Sodium-dependent serotonin transporter	IC50	=	1.1	nM	8.96	Binding affinity to human 5-HT transporter by radioligand displacement assay	23466604
Serotonin (5-HT) receptor	IC50	=	1.1	nM	8.96	Inhibition of 5HT receptor (unknown origin)	28849908
Ileum	Kd	=	1.259	nM	8.9	Anticholinergic effect in guinea pig ileum assessed as inhibition of acetylcholi...	533885
Alpha-1A adrenergic receptor	IC50	=	1.7	nM	8.77	Inhibition of binding of [3H]imipramine to imipramine receptor in rat brain	1976813
Sodium-dependent serotonin transporter	Ki	=	1.9	nM	8.72	Displacement of [3H] imipramine from human recombinant 5-HT transporter measured...	31112891
Sodium-dependent serotonin transporter	Ki	=	2.0	nM	8.7	Displacement of [3H]citalopram from human SERT expressed in HEK293 cell membrane...	27865645
Sodium-dependent serotonin transporter	IC50	=	2.0	nM	8.7	Binding affinity to human serotonin 5-HT transporter by radioligand displacement...	23582449
Sodium-dependent serotonin transporter	Ki	=	2.1	nM	8.68	Displacement of [3H]imipramine from human recombinant SERT expressed in CHO cell...	24805037
Sodium-dependent serotonin transporter	Ki	=	2.1	nM	8.68	Displacement of [3H]imipramine from human SERT expressed in CHO cells	25557493
Sodium-dependent serotonin transporter	Ki	=	2.5	nM	8.6	Displacement of [3H]-imipramine from human serotonin transporter expressed in HE...	31586817
Sodium-dependent serotonin transporter	IC50	=	2.6	nM	8.59	Inhibition of human SERT W103A mutant expressed in HEK293 MSR cells assessed as ...	27160055
Sodium-dependent serotonin transporter	Ki	=	3.2	nM	8.49	Displacement of radiolabeled imipramine from human SERT	18983139
Sodium-dependent serotonin transporter	IC50	=	3.5	nM	8.46	Binding affinity to SERT (unknown origin) by radioligand binding assay	23919353

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1404
23378628	10.1124/dmd.112.050054	ADMET	16
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
7328600	10.1021/jm00140a013	Rattus norvegicus	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
10649973	10.1021/jm980333v	Mus musculus	10
19679379	10.1016/j.ejmech.2009.07.014	Mus musculus	9
6103958	10.1021/jm00178a009	Mus musculus	9
17418579	10.1016/j.bmc.2007.03.040	ADMET	9
1335075	10.1021/jm00102a004	Mus musculus	9
17517514	10.1016/j.bmc.2007.05.017	Mus musculus	9
6103959	10.1021/jm00178a010	Mus musculus	9
6167716	10.1021/jm00135a006	ADMET	8
1246052	10.1021/jm00223a010	Mus musculus	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
7265119	10.1021/jm00135a018	Mus musculus	7
6716399	10.1021/jm00371a011	Mus musculus	7
17321139	10.1016/j.bmc.2007.02.018	Mus musculus	6
20060623	10.1016/j.ejmech.2009.11.053	Mus musculus	6
4067998	10.1021/jm00149a031	Mus musculus	6

Data from ChEMBL 36 via Core Engine